Your thoughts really struck a chord with me, thanks for sharing. I’m in the early days of my sabbatical and can definitely see the different pillars you mention.
What is interesting for me is the reaction of the “outside” world - it seems there is a big divide between those of us transitioning into portfolio careers and the people looking at things in a more traditional way. I think the societal pressure is something not to be underestimated in this change, especially in some cultures. Maybe an angle for your to consider, too?
Thanks so much for reading and commenting! I think the reaction of the outside world is one of the hardest parts. For me personally, but also for many people I’ve spoken to. There’s often this subtle sense of societal devaluation, even when it’s not intentional.
I placed that theme - the societal pressure - within the Community pillar (you can see it under the transition struggles). It’s also why I believe community is such an underestimated catalyst. Finding people who think like you, are in a similar transition, or can simply listen and understand, gives a completely new perspective and is often what helps you keep going. 🙂
It’s like you’ve been reading my journal entries for the past 6 months haha. Thanks for clearly unraveling such a robust topic, Iwana.
I feel infinitely more free in carving my my creative pursuit the way I want to. No matter how many shapes and sizes it adopts at a time over time, it feels real and embodies expressions of me.
In the 2+ years that I worked full-time after graduating, I amassed 8 internationally recognised awards in 5 months. I was hoping to leave the establishment with at least 2 or something. So, ooo la la I guess, but those awards no longer resonate with the magnitude of my creative offerings. They’re now an embellishment for my portfolio — a “proof of competence” if you will — and a gravestone for my desire to do brand design (or frankly, just creative production constantly under someone else’s sway) on-demand.
If I could manage that in a space and time that also couldn’t accommodate my neurodivergence as well as I needed … well, shoot, imagine what I could do with my own agency!
I’m in the early portfolio career building stage. So, there’s a lot of experiences, thoughts, sentiments, ideas, whatevers that have become SO MUCH clearer with time and intuitive practice. The financial aspect is temporarily biting me in the bums. However, I am without doubt that my financial freedom will grow prosperously alongside my creative freedom.
Haha, love that! Seems like our journal entries capture what so many people feel during this transition. 🙂 Sounds like you’re on such an interesting journey! I’m sure it’ll all come together step by step.
Glad you enjoyed it! It’s not easy but can definitely be learned! You can check out the indepth articles on the five pillars if you’re curious to learn more. 🙂
as someone from the developing world, I worked my way up from freelancing for dirt cheap to now charging $50/hr, moved abroad, only to go have a 9-5 job that disappeared when i started to see the sign of burnout. Now i promised myself i'm never going back to charging lesser than that AND giving my soul to a company. I have the community, the identity and vision. I'm struggling with the positioning, and figuring out my other strengths. I cannot wait to see what the future has in store for me :)
As an introvert, I thank you for the conversations and research you have done to put words on the struggles essentially.
I quit my job (after a burnout) a year ago and only now I have created my visual map, my second brain, re-defining my identity and vision. My next step is to figure out ways to grow without falling into the trap of freelancing aka having 100 bosses instead of 1 for a salary job.
Thank you also for diving into each pillar in more detail.
It’s great to hear you’re already moving toward a life that fits you better. And yes, that trap is real, but you seem very aware of it, which is exactly what makes it possible to navigate differently. 🙂
Thanks for putting this into words and sharing with us all. It’s no surprise it’s resonating with so many. All feelings that are familiar and a framework that helps with the shift from the old.
Excellent summary, and many points resonate with me. The identify part is challenging but I realize that owning your own firm is just as impressive as being a cog in one. Also, one challenge is squirreling away nuts before you leap only to push the goal line just to squirrel away even more nuts at the expense of your health and sanity. It's part of the process I assume!
Yeah I guess the trap of endless preparation is real. Over-optimizing for future security while sacrificing present well-being. I think a big part of the transition is learning to build inner security instead: confidence in our skills, trust in the path, perspective on the real cost of staying and a rational look at whether the “worst case” is actually that bad.
Damn, you took the words right out of me haha. Especially the part about identity - it's so true. Really like the idea of exchanging pieces with eachother in a portfolio career
Amazing, that's such a great compliment, thank you! 🙂 Identity really seems to be the part that hits people the hardest…
What I love about the portfolio career path is exactly that you don’t have to choose one thing forever. You get to evolve, mix different interests over time and build a career that grows with you.
You articulated this framework so well! I’ve been on this journey for a few years now. I didn’t struggle with the identity or community parts because I never felt like I quite fit into corporate; the financial aspect is the most challenging. My sabbatical solidified that I never wanted to be a full time employee again, and I’ve found creating my own portfolio career to be much more fulfilling.
Thanks, Nyamwathi - appreciate it! I believe there’s no one-size-fits-all career model, but for a long time we acted as if there was (and there maybe weren’t as many alternatives). That’s changing now, and many are realizing they might not fit the traditional corporate mold - they just hadn’t questioned it or found the courage to try something different. Glad to hear you’re finding your own, more fulfilling direction! 🙂
I've struggled most with identity and money. I've spent so many years conditioning on the external validation that a company name or title provides, that, once I was 'free' of it, I kept on telling myself a lot of limiting beliefs about what I can and cannot do and identify as. Money-wise, I think the struggle has been on setting my worth vs the worth of a company (not sure if that makes sense).
Thanks for shining a light on these darker spaces - and I'm so excited to read your next editions!
Thanks so much for sharing, Katharina! Super interesting insights, and I can totally relate. Will make sure to reflect more in-depth on everything in the next editions. 🙂
Your thoughts really struck a chord with me, thanks for sharing. I’m in the early days of my sabbatical and can definitely see the different pillars you mention.
What is interesting for me is the reaction of the “outside” world - it seems there is a big divide between those of us transitioning into portfolio careers and the people looking at things in a more traditional way. I think the societal pressure is something not to be underestimated in this change, especially in some cultures. Maybe an angle for your to consider, too?
Thanks so much for reading and commenting! I think the reaction of the outside world is one of the hardest parts. For me personally, but also for many people I’ve spoken to. There’s often this subtle sense of societal devaluation, even when it’s not intentional.
I placed that theme - the societal pressure - within the Community pillar (you can see it under the transition struggles). It’s also why I believe community is such an underestimated catalyst. Finding people who think like you, are in a similar transition, or can simply listen and understand, gives a completely new perspective and is often what helps you keep going. 🙂
It’s like you’ve been reading my journal entries for the past 6 months haha. Thanks for clearly unraveling such a robust topic, Iwana.
I feel infinitely more free in carving my my creative pursuit the way I want to. No matter how many shapes and sizes it adopts at a time over time, it feels real and embodies expressions of me.
In the 2+ years that I worked full-time after graduating, I amassed 8 internationally recognised awards in 5 months. I was hoping to leave the establishment with at least 2 or something. So, ooo la la I guess, but those awards no longer resonate with the magnitude of my creative offerings. They’re now an embellishment for my portfolio — a “proof of competence” if you will — and a gravestone for my desire to do brand design (or frankly, just creative production constantly under someone else’s sway) on-demand.
If I could manage that in a space and time that also couldn’t accommodate my neurodivergence as well as I needed … well, shoot, imagine what I could do with my own agency!
I’m in the early portfolio career building stage. So, there’s a lot of experiences, thoughts, sentiments, ideas, whatevers that have become SO MUCH clearer with time and intuitive practice. The financial aspect is temporarily biting me in the bums. However, I am without doubt that my financial freedom will grow prosperously alongside my creative freedom.
Haha, love that! Seems like our journal entries capture what so many people feel during this transition. 🙂 Sounds like you’re on such an interesting journey! I’m sure it’ll all come together step by step.
I love reading more stuff on portfolio careers it's a mindset that quite hard to jump into
Glad you enjoyed it! It’s not easy but can definitely be learned! You can check out the indepth articles on the five pillars if you’re curious to learn more. 🙂
as someone from the developing world, I worked my way up from freelancing for dirt cheap to now charging $50/hr, moved abroad, only to go have a 9-5 job that disappeared when i started to see the sign of burnout. Now i promised myself i'm never going back to charging lesser than that AND giving my soul to a company. I have the community, the identity and vision. I'm struggling with the positioning, and figuring out my other strengths. I cannot wait to see what the future has in store for me :)
Thanks for sharing your story! I’m sure there’s going to be great things for you in store in the future 🙂
As an introvert, I thank you for the conversations and research you have done to put words on the struggles essentially.
I quit my job (after a burnout) a year ago and only now I have created my visual map, my second brain, re-defining my identity and vision. My next step is to figure out ways to grow without falling into the trap of freelancing aka having 100 bosses instead of 1 for a salary job.
Thank you also for diving into each pillar in more detail.
Thank you so much and I’m glad it helps!
It’s great to hear you’re already moving toward a life that fits you better. And yes, that trap is real, but you seem very aware of it, which is exactly what makes it possible to navigate differently. 🙂
Love all of this! Could not agree more 🙏🏼🙏🏼
Thanks, Fiona! So glad you enjoyed it! 🙂
Thanks for putting this into words and sharing with us all. It’s no surprise it’s resonating with so many. All feelings that are familiar and a framework that helps with the shift from the old.
Thanks, James! Really glad it seems to resonate and help! 🙂
Excellent summary, and many points resonate with me. The identify part is challenging but I realize that owning your own firm is just as impressive as being a cog in one. Also, one challenge is squirreling away nuts before you leap only to push the goal line just to squirrel away even more nuts at the expense of your health and sanity. It's part of the process I assume!
Yeah I guess the trap of endless preparation is real. Over-optimizing for future security while sacrificing present well-being. I think a big part of the transition is learning to build inner security instead: confidence in our skills, trust in the path, perspective on the real cost of staying and a rational look at whether the “worst case” is actually that bad.
Damn, you took the words right out of me haha. Especially the part about identity - it's so true. Really like the idea of exchanging pieces with eachother in a portfolio career
Amazing, that's such a great compliment, thank you! 🙂 Identity really seems to be the part that hits people the hardest…
What I love about the portfolio career path is exactly that you don’t have to choose one thing forever. You get to evolve, mix different interests over time and build a career that grows with you.
This is great! Thanks for writing it!
Thanks, David! Glad you enjoyed it and thanks for letting me know! 🙂
You articulated this framework so well! I’ve been on this journey for a few years now. I didn’t struggle with the identity or community parts because I never felt like I quite fit into corporate; the financial aspect is the most challenging. My sabbatical solidified that I never wanted to be a full time employee again, and I’ve found creating my own portfolio career to be much more fulfilling.
Thanks, Nyamwathi - appreciate it! I believe there’s no one-size-fits-all career model, but for a long time we acted as if there was (and there maybe weren’t as many alternatives). That’s changing now, and many are realizing they might not fit the traditional corporate mold - they just hadn’t questioned it or found the courage to try something different. Glad to hear you’re finding your own, more fulfilling direction! 🙂
Thanks for articulating this journey for folks!
Loved your split of pillars, indeed it's very much a psychological game!
Thanks, Apoorvaa, for taking the time to let me know. 🙂 I think it is! One that we can master though.
Couldn't agree more. 'Unbundling the job' perfectly captures it.
Thank you! Glad it resonated 🙂
This really resonates.
I've struggled most with identity and money. I've spent so many years conditioning on the external validation that a company name or title provides, that, once I was 'free' of it, I kept on telling myself a lot of limiting beliefs about what I can and cannot do and identify as. Money-wise, I think the struggle has been on setting my worth vs the worth of a company (not sure if that makes sense).
Thanks for shining a light on these darker spaces - and I'm so excited to read your next editions!
Thanks so much for sharing, Katharina! Super interesting insights, and I can totally relate. Will make sure to reflect more in-depth on everything in the next editions. 🙂
Love this approach. I liked it enough that I am going to read again. I think you are to something here.
Thank you, Danielle! That's a great compliment 🙂. I'm very excited about it too, but even better to hear it from others! 👏
This is absolutely brilliant. Thanks for this.
Thank you, Sara! So glad to hear! 🥹🙏🏻